Transition metal-catalyzed [5+2] cycloadditions of 2-substituted-1-vinylcyclopropanes: Catalyst control and reversal of regioselectivity

Authors
Wender, PA Dyckman, AJ
Citation
Pa. Wender et Aj. Dyckman, Transition metal-catalyzed [5+2] cycloadditions of 2-substituted-1-vinylcyclopropanes: Catalyst control and reversal of regioselectivity, ORG LETT, 1(13), 1999, pp. 2089-2092
Citations number
11
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
1
Issue
13
Year of publication
1999
Pages
2089 - 2092
Database
ISI
SICI code
1523-7060(199912)1:13<2089:TM[CO2>2.0.ZU;2-U
Abstract
[GRAPHICS] Studies on the stereo- and regioselectivity of rhodium(I) catalyzed [5 + 2] cycloadditions of 2-substituted-1-vinylcyclopropanes are described. The re lative stereochemistry of vicinal cyclopropane substituents is found to be conserved in these reactions, translating into distinct 1,4- or 1,5-stereor elationships in the cycloadducts. Exceptional regioselectivity in cycloprop ane bond cleavage and even reversal of cleavage selectivity can be obtained through judicious selection of substituents and/or catalyst.